


Roommate

by lovingsmutandfluff



Series: Tumblr Ficlets/Drabbles [388]
Category: Supernatural
Genre: Alternate Universe - College/University, Dean is a Little Shit, Feminization, Humiliation, Humiliation kink, M/M, Mildly Dubious Consent, Panty Kink, Smut, Teasing, just in case
Language: English
Status: Completed
Published: 2015-09-15
Updated: 2015-09-15
Packaged: 2018-04-20 21:26:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 953
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4802765
Author URL: https://archiveofourown.org/users/lovingsmutandfluff/pseuds/lovingsmutandfluff
Summary: <blockquote class="userstuff">
              <p>Prompt: Can you write a little thing where dean and cas are new roommates but dean is like really cocky and annoyingish and him and his friends won't let cas go to sleep unless he does all the humiliating things they make him do</p>
            </blockquote>





	Roommate

**Author's Note:**

> I don't take prompts here, only on lovingsmutandfluff.tumblr.com

Cas groaned, hearing the laughing again.

“Guys, seriously…” He grunted. “I need to sleep, can you people go to one of the different dorms?”

“Little Cas need his beauty rest?” Dean grinned, moving over to Cas. “Needs some sleep for his big test in the morning?”

“Yeah. I do need sleep. I do have a test tomorrow, I would enjoy it if you got your friends out of here.” Cas said, trying to stare down his cocky roommate. Apparently Dean’s former roommate transferred out. Cas understood why. And Cas had been unlucky enough for him roommate to graduate, leaving him with an available space to be filled.

“I don’t think I can do that just yet, Cas.”

“And why’s that?” Cas asked at the annoying Winchester.

“Cause the fun is just beginning. Get up Cas.”

“No.”

“Come on Cas. You get up, and do what I say, and we’ll leave, and let you sleep.”

Cas stared at Dean, debating on whether to listen to the guy.

“Fine.” Cas said, giving in, and standing up. “What do you want me to do?”

“Strip. To your underwear at least.” Dean said, leaning back on his desk, and Dean’s friends started laughing and cheering.

“What? Are you insane?”

“Wanna go to sleep, angel?” Dean asked, and Cas clenched his fists at the nickname. “Strip down.”

Cas grunted, turning slightly red, and he removed his shirt.

“Shit, ever tried to tan before, Cas?” Dean asked, eyes roaming Cas’ chest.

“Have you?” Cas retorted, and Dean’s friends laughed, while Dean gave Cas a look.

“Pants too, buddy.” Dean said, crossing his arms.

Cas hesitantly put his fingers around the waist of his pajama pants.

“Scared?” Dean asked, smirking.

Cas pushed them down, and heard the teases and taunts as the group saw the starch white underwear he was wearing.

“Damn Cas. Not even briefs?”

“I do own some, I just had to grab something to wear.” Cas said, flushing red again. He looked at Dean, watching his eyes roam around Cas’ body, and if Cas was stupider, he would have asked if Dean was checking him out. Dean himself wasn’t that bad looking, but his cocky attitude was grating on Cas’ nerves.

“Alright Cas. Next thing.” Dean said.

“Next?”

“Of course.” Dean said. Cas watched him move away, reaching into a small duffel bag and pulling out a pair of black satin and lace panties. He tossed them over to Cas, who caught them and looked at Dean in horror. “Put them on.”

“But….but…you’re fucking kidding.” Cas stuttered.

“Not if you want sleep dude.” Dean said.

“I’m not taking my underwear off in front of everyone! And I rather have you guys being asses and keeping me up if it means that you won’t take pictures of this.”

“Who said anything about pictures? I didn’t.” Dean said. “Scouts honor, dude. No pictures. Right guys?” Dean asked.

A round of agreement emerged from the group and Dean grinned.

“We’ll turn around, but you gotta put on the panties.” Dean turned around, and the group followed suit, and Cas looked down at the black fabric, before he pushed down his underwear and put on the panties, surprised at how good they felt, and he was pretty sure he felt himself hardening slightly.

Cas made sure that he was tucked inside the panties, nothing showing, and he cleared his throat.

“I’m….I’m in them.” He said softly. Dean turned around and grinned, and Cas was certain that Dean was probably checking him out, while the others hooted and laughed.

“Awesome.” Dean said. “Like I said, no pictures will be taken of you. But turn around and show off.”

“Dean…” Cas said, embarrassed, cheeks and ears turning red.

“Almost done Cas. Just do a three-sixty.”

Cas turned around slowly, and then stood back in the same position he was, and he couldn’t deny the small bulge in Dean’s pants.

“One more…well, two more things Cas.” Dean said.

“And what’s that?”

Dean went back to the duffel, pulling out stockings and a skirt.

“On they go, angel.” Dean said, tossing the clothing over. “And we aren’t gonna look away this time.”

Cas took the skirt first, pulling it on, and looking up at Dean with a red face, but he could feel arousal shooting in him, only making him more embarrassed. Cas got the skirt on, thanking that the small fabric was covering his semi-hard on, and he started pulling up the stockings next.

When they were on, he looked up at Dean, while the guys around them laughed.

“Turn around three-sixty again Cas.” Dean said, not really laughing like the others.

Cas started turning again, when he was facing away from the group.

“Freeze for a sec. Lift your arms against the posts of the bed.

Cas did as Dean said, and let out a shaky nervous breath, hearing the cat calls.

"OK…you can turn the rest of the way.”

Cas did and watched Dean.

“See? That wasn’t so bad.” Dean grinned. “We’ll leave you alone now. Let’s get to a different room. I’ll be right with you guys. Bathroom break.” Dean said, watching his friends head out, saying what room they would be in.

The others left and Dean turned to Cas. “You can change back now, angel. Put the things that I gave you back by the duffel bag, and you can go to bed.”

Dean turned and walked into the bathroom, and Cas got changed quickly, shutting the light off, and relaxing in his bed.

He wasn’t sure, but he was pretty certain that he heard soft gasps from the bathroom, and Cas squirmed slightly, growing aroused, realizing what the show had all been about.


End file.
